Dichloroacetic Acid → (+)-alpha-Terpineol

HRID 1719839Notes

Reaction equation

HRID 1719839 reaction equation
ClC(Cl)C(O)=[O:4].[CH3:7][C:8]1[C@@H:13]2[C:14]([CH3:16])([CH3:15])[C@@H:11]([CH2:12]2)[CH2:10][CH:9]=1>O>[CH3:7][C:8]1[CH2:13][CH2:12][C@@H:11]([C:14]([OH:4])([CH3:16])[CH3:15])[CH2:10][CH:9]=1

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 82227alpha-Pinene, (+)-

Product 1

HCID 442501(+)-alpha-TerpineolYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Followiwng a procedure described in Matsubara, et al., Chem. Abstr., 84:165069b (1976), 64.5 g of dichloroacetic acid was added dropwise over 20 minutes at 5°-6° C. to a magnetically stirred mixture of 68.0 g of (+)-alpha-pinene ([alpha]D +47.1°) and 9.0 g of water. after stirring overnight at 5°-30° C. (ice allowed to melt slowly), the mixture was extracted with 400 ml of methylene chloride. The extract was washed successively with water, aqueous potassium carbonate solution and water, dried and Claisen distilled at 4 mm to give 11.2 g of forecut, b.p. 40°-71° C. and 47.5 g of the desired (+)-alpha-terpineol, b.p. 71°-83° C. Redistillation through a micro Vigreaux column gave 40.5 g of (+)-alpha-terpineol with [alpha]D +79.3° (CHCl3), b.p. 58°-60° C. (1 mm).

Workup

  1. extractionwas extracted with 400 ml of methylene chloride
  2. washThe extract was washed successively with water, aqueous potassium carbonate solution and water
  3. customdried
  4. distillationClaisen distilled at 4 mm

Sources & evidence

ORD record
ord-1e8602b849b64f86b4ae6cfeb2b5869c
Source dataset
uspto-grants-1985_09
Patent number
US04542244

Reaction notes

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